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The built-in SMTP delivery channel doesn't support authentication or TLS. To send email you'll either need to find another server through which to send your notifications, or implement a custom delivery channel.

You can relay through the STMP server built into Windows Server per this blog post:

The required settings "TSL/SSL", ports, etc are specific to each provider. You would need to check their documentation.

For example:

A quick search found the following:
http://help.yahoo.com/l/us/yahoo/smallbusiness/bizmail/pop/pop-33.html
http://windows.microsoft.com/en-US/hotmail/send-receive-email-from-mail-client

Each company will provide the specific smpt/pop info for their service and you will need to adjust your settings accordingly. If you're not sure what these settings mean I suggest that you take a step back and learn a little about how IP Addresses,
ports, TLS and SMTP gateways work. (I know this isn't the best answer, but sometimes it helps to understand the underlying components.)

The long and short:
TLS and SSL are encryption tunnels between 2 points (ex: your computer and one of Google's servers). How they shake hands and implement that tunnel are what differentiate TLS, SSL (and the various versions of each).

The required settings "TSL/SSL", ports, etc are specific to each provider. You would need to check their documentation.

For example:

A quick search found the following:
http://help.yahoo.com/l/us/yahoo/smallbusiness/bizmail/pop/pop-33.html
http://windows.microsoft.com/en-US/hotmail/send-receive-email-from-mail-client

Each company will provide the specific smpt/pop info for their service and you will need to adjust your settings accordingly. If you're not sure what these settings mean I suggest that you take a step back and learn a little about how IP Addresses,
ports, TLS and SMTP gateways work. (I know this isn't the best answer, but sometimes it helps to understand the underlying components.)

The long and short:
TLS and SSL are encryption tunnels between 2 points (ex: your computer and one of Google's servers). How they shake hands and implement that tunnel are what differentiate TLS, SSL (and the various versions of each).

Unfortunately SSRS appears to be using an old email library. TLS is newer then SSL and for whatever reason MS did not update their email library in SSRS to support it (or at the very least expose the TLS setting).

As a result we're forced to use these hacks/work arounds to get SSRS to connect to services that use TLS.

Your email provider (Google, Hotmail, Exchange, etc) can configure their smtp server security in any number of ways. Because Google (in this case) chose to go with the newer (and more secure) TLS, we (the programmer or client application) are on the
hook for supporting it. There is no way to connect by any other means/protocol, and again MS has yet to update their code to add support.

Is it possible for MS to add TLS support to SSRS? Absolutely! I've written my own .Net email libraries and it was consider a critical feature! They just haven't done so or exposed it. In the end we're stuck with these workarounds.